Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source

Muhammad Siddique Ahmad; Zahid Shafiq; Kamel Meguellati

doi:10.1055/a-1770-8592

Synthesis, Table of Contents

Synthesis 2022; 54(13): 3077-3084
DOI: 10.1055/a-1770-8592

paper

Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source

Muhammad Siddique Ahmad ∗

^aSchool of Pharmacy, Jinan University, 855 Xingye Avenue East, Guangzhou, 511436, P. R. of China

,

Zahid Shafiq

^bInstitute of Chemical Sciences, Bhahauddin Zakariya University, Multan, 60800, Pakistan

,

Kamel Meguellati ∗

^aSchool of Pharmacy, Jinan University, 855 Xingye Avenue East, Guangzhou, 511436, P. R. of China

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Abstract

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Abstract

The present study describes the one-pot palladium-catalyzed cyanation of commercially available aryldiazonium tetrafluoroborate derivatives with 2-(piperidin-1-yl)acetonitrile (an organic cyano reagent) under mild conditions. This process utilizes a Pd/(Me₃Si)₂ system and is applied to a wide scope of aromatic diazonium substrates to give the corresponding nitrile-containing products in moderate to high yields (59–92%). This methodology is employed for the preparation of etravirine, a drug used for the treatment of HIV, and for transformations of 1H-indole-2-carbonitrile into compounds that are used as a NMDA receptor antagonists and that have high potential against mutant HIV strains. The mechanism proposed for this Pd-catalyzed cyanation involves cyanide ions, as confirmed using indicator paper.

Key words

C–CN cleavage - cyanation - Pd catalyst - coupling reaction - organic CN source

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References

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